pentamidine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2090 100-33-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • pentamidine isetionate
  • pentamidine diisethionate
  • pentamidine
  • pentamidine isethionate
  • pentamidin
  • pentamidine mesylate
  • pentamidine mesilate
Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.
  • Molecular weight: 340.43
  • Formula: C19H24N4O2
  • CLOGP: 2.31
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 4
  • TPSA: 118.20
  • ALOGS: -4.16
  • ROTB: 10

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.28 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 100 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 12 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 11.75 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 53 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 74 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.09 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 25 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 16, 1984 FDA FRESENIUS KABI USA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Pneumocystis jirovecii pneumonia 167.67 22.08 61 4762 16317 53327926
Aplastic anaemia 104.14 22.08 36 4787 8285 53335958
Nocardiosis 84.00 22.08 22 4801 1965 53342278
Toxoplasmosis 75.90 22.08 19 4804 1417 53342826
Cytomegalovirus viraemia 71.88 22.08 24 4799 4967 53339276
Febrile neutropenia 71.84 22.08 66 4757 104870 53239373
Hypoalbuminaemia 66.69 22.08 28 4795 10908 53333335
Antinuclear antibody negative 63.82 22.08 12 4811 228 53344015
Antithrombin III 60.65 22.08 11 4812 170 53344073
Herpes simplex reactivation 58.26 22.08 12 4811 370 53343873
Coombs positive haemolytic anaemia 58.01 22.08 12 4811 378 53343865
Delayed graft function 56.47 22.08 14 4809 1003 53343240
Lymphopenia 52.23 22.08 27 4796 16816 53327427
Graft versus host disease 49.40 22.08 20 4803 7102 53337141
Gastritis haemorrhagic 42.07 22.08 12 4811 1472 53342771
Antiphospholipid syndrome 40.01 22.08 12 4811 1754 53342489
Rhodococcus infection 39.44 22.08 7 4816 95 53344148
Focal myositis 38.20 22.08 6 4817 36 53344207
Cytomegalovirus infection 37.84 22.08 23 4800 19516 53324727
Cryptosporidiosis infection 37.72 22.08 8 4815 285 53343958
Complex regional pain syndrome 37.29 22.08 12 4811 2211 53342032
Pyrexia 36.78 22.08 99 4724 403094 52941149
Escherichia bacteraemia 36.35 22.08 13 4810 3295 53340948
Leukopenia 35.03 22.08 38 4785 73425 53270818
Neutropenia 34.66 22.08 56 4767 159129 53185114
Renal tubular necrosis 34.52 22.08 18 4805 11401 53332842
Mycobacterium avium complex infection 34.29 22.08 12 4811 2856 53341387
Encephalitis cytomegalovirus 32.36 22.08 8 4815 566 53343677
Enterococcal infection 31.96 22.08 15 4808 7583 53336660
Cytokine release syndrome 31.00 22.08 15 4808 8114 53336129
Anxiety disorder 30.43 22.08 12 4811 3978 53340265
Ectropion 29.62 22.08 6 4817 170 53344073
Cytomegalovirus gastroenteritis 28.70 22.08 6 4817 199 53344044
Pancytopenia 28.49 22.08 38 4785 90890 53253353
Acute kidney injury 26.86 22.08 66 4757 253802 53090441
Erysipelas 26.42 22.08 13 4810 7288 53336955
Malacoplakia 26.35 22.08 5 4818 100 53344143
Blood phosphorus decreased 26.33 22.08 11 4812 4226 53340017
Thrombotic microangiopathy 26.18 22.08 14 4809 9323 53334920
Pain 25.04 22.08 11 4812 588387 52755856
Pleuritic pain 24.13 22.08 12 4811 6884 53337359
Cytopenia 23.63 22.08 13 4810 9157 53335086
Acute febrile neutrophilic dermatosis 23.09 22.08 9 4814 2892 53341351
Bone marrow failure 22.64 22.08 20 4803 30095 53314148

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Nocardiosis 142.04 19.34 46 6817 3685 32502978
Toxoplasmosis 100.82 19.34 28 6835 1321 32505342
Febrile bone marrow aplasia 83.35 19.34 39 6824 8376 32498287
Cerebral toxoplasmosis 74.86 19.34 23 6840 1549 32505114
Pneumocystis jirovecii pneumonia 56.35 19.34 40 6823 18830 32487833
Respiratory failure 54.47 19.34 88 6775 107094 32399569
Pancytopenia 52.03 19.34 79 6784 91156 32415507
Aplastic anaemia 51.65 19.34 27 6836 7346 32499317
Cytokine release syndrome 50.67 19.34 33 6830 13502 32493161
Mucosal inflammation 49.29 19.34 47 6816 33387 32473276
Glomerulosclerosis 48.61 19.34 14 6849 753 32505910
Oesophagitis 47.01 19.34 31 6832 12950 32493713
Pyrexia 45.29 19.34 159 6704 319809 32186854
Immune reconstitution inflammatory syndrome 45.10 19.34 27 6836 9532 32497131
Botulism 44.24 19.34 10 6853 200 32506463
Kidney fibrosis 41.15 19.34 16 6847 2179 32504484
Haematopoietic stem cell mobilisation 40.30 19.34 9 6854 170 32506493
Graft versus host disease 39.59 19.34 26 6837 10780 32495883
Cystitis haemorrhagic 39.49 19.34 20 6843 5094 32501569
Neutropenia 39.12 19.34 90 6773 142085 32364578
Acanthamoeba infection 35.79 19.34 10 6853 482 32506181
Haemophagocytic lymphohistiocytosis 33.76 19.34 24 6839 11311 32495352
Pulmonary nocardiosis 33.48 19.34 10 6853 611 32506052
Venoocclusive liver disease 32.67 19.34 20 6843 7345 32499318
Staphylococcal bacteraemia 32.39 19.34 20 6843 7456 32499207
Aspergillus infection 31.05 19.34 23 6840 11551 32495112
Cytomegalovirus infection 30.51 19.34 32 6831 25432 32481231
Thyroid gland abscess 29.97 19.34 6 6857 65 32506598
Bronchospasm 29.90 19.34 22 6841 10933 32495730
Cytomegalovirus viraemia 29.16 19.34 18 6845 6709 32499954
Cytomegalovirus chorioretinitis 27.52 19.34 14 6849 3598 32503065
Generalised oedema 27.35 19.34 22 6841 12461 32494202
Infectious thyroiditis 27.19 19.34 6 6857 107 32506556
Febrile neutropenia 26.80 19.34 70 6793 119496 32387167
Death 26.66 19.34 25 6838 382492 32124171
Genitourinary tract infection 26.45 19.34 6 6857 122 32506541
Stenotrophomonas infection 26.29 19.34 11 6852 1809 32504854
Folliculitis 24.98 19.34 14 6849 4366 32502297
Parvovirus B19 infection 24.88 19.34 8 6855 625 32506038
Kaposi's sarcoma 24.80 19.34 9 6854 1013 32505650
Bacterial toxaemia 24.28 19.34 6 6857 178 32506485
Face oedema 24.21 19.34 20 6843 11755 32494908
Urogenital infection bacterial 24.07 19.34 5 6858 66 32506597
Central nervous system lesion 23.75 19.34 15 6848 5817 32500846
Mycobacterium fortuitum infection 23.27 19.34 6 6857 212 32506451
Purpura non-thrombocytopenic 23.23 19.34 5 6858 79 32506584
B-cell aplasia 23.11 19.34 5 6858 81 32506582
Photodermatosis 22.42 19.34 7 6856 497 32506166
Multiple organ dysfunction syndrome 22.31 19.34 47 6816 69807 32436856
Chronic graft versus host disease 22.14 19.34 13 6850 4427 32502236
Pancreatitis acute 22.03 19.34 28 6835 27307 32479356
Elbow synostosis 21.54 19.34 4 6859 28 32506635
Synostosis 21.45 19.34 5 6858 115 32506548
Tongue disorder 21.39 19.34 13 6850 4711 32501952
Herpes zoster 21.28 19.34 30 6833 32311 32474352
Demodicidosis 19.93 19.34 5 6858 158 32506505
Staphylococcal infection 19.74 19.34 29 6834 32410 32474253
Pulmonary necrosis 19.68 19.34 6 6857 393 32506270

Pharmacologic Action:

SourceCodeDescription
ATC P01CX01 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
AGENTS AGAINST LEISHMANIASIS AND TRYPANOSOMIASIS
Other agents against leishmaniasis and trypanosomiasis
FDA EPC N0000175485 Antiprotozoal
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000935 Antifungal Agents
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
MeSH PA D014344 Trypanocidal Agents
CHEBI has role CHEBI:36335 trypanosomicidal agents
CHEBI has role CHEBI:35703 Xenobiotic
CHEBI has role CHEBI:35718 antifungal drug
CHEBI has role CHEBI:60643 N-methyl-D-aspartate receptor antagonists
CHEBI has role CHEBI:63673 chemokine receptor 5 antagonists
CHEBI has role CHEBI:67079 antiinflammatory agents
CHEBI has role CHEBI:76395 histone acetyltransferase (EC 2.3.1.48) inhibitor
CHEBI has role CHEBI:136651 S100B inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
African trypanosomiasis indication 27031003 DOID:10112
Pneumocystosis jiroveci pneumonia indication 415125002 DOID:11339
Pneumocystis Carinii Pneumonia Prevention indication
Visceral leishmaniasis off-label use 186803007 DOID:9146
Cutaneous leishmaniasis off-label use 240637006 DOID:9111
Hypocalcemia contraindication 5291005
Hyperkalemia contraindication 14140009
Torsades de pointes contraindication 31722008
Dehydration contraindication 34095006
Hypertensive disorder contraindication 38341003 DOID:10763
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:557
Liver function tests abnormal contraindication 166603001
Hypomagnesemia contraindication 190855004
Asthma contraindication 195967001 DOID:2841
Acute pancreatitis contraindication 197456007 DOID:2913
Disease of liver contraindication 235856003 DOID:409
Toxic nephropathy contraindication 236514003
Hypoglycemic disorder contraindication 237630007
Anemia contraindication 271737000 DOID:2355
Thrombocytopenic disorder contraindication 302215000 DOID:1588

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.38 Basic
pKa2 10.78 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Muscarinic acetylcholine receptor M2 GPCR Ki 6.30 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 6.29 DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2 Ion channel Ki 4.89 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.66 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 6.33 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 5.77 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 5.87 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 6.66 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 5.68 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.60 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 6.31 DRUG MATRIX
Amine oxidase [flavin-containing] A Enzyme IC50 6.10 DRUG MATRIX
Plasminogen Enzyme IC50 5.44 CHEMBL
Trypsin-1 Enzyme Ki 5.64 CHEMBL
Coagulation factor X Enzyme IC50 4.98 CHEMBL
Suppressor of tumorigenicity 14 protein Enzyme Ki 5.94 CHEMBL
Protein S100-B Cytosolic other Kd 6 CHEMBL
Protein arginine N-methyltransferase 1 Enzyme IC50 4.09 CHEMBL
Solute carrier family 22 member 1 Transporter IC50 4.66 CHEMBL
Amiloride-sensitive amine oxidase [copper-containing] Enzyme Ki 6.54 CHEMBL
Solute carrier family 22 member 2 Transporter IC50 5.92 CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 6.39 CHEMBL
Multidrug and toxin extrusion protein 2 Transporter IC50 5.57 CHEMBL
Solute carrier family 22 member 3 Transporter IC50 5.02 CHEMBL
Glutamate NMDA receptor; GRIN1/GRIN2A Ion channel IC50 6.14 CHEMBL
Spermidine/spermine N(1)-acetyltransferase 1 Enzyme Ki 5.70 CHEMBL
Protein-tyrosine phosphatase 4A3 Enzyme IC50 4.27 CHEMBL
Protein tyrosine phosphatase type IVA 2 Enzyme IC50 6.52 CHEMBL
Protein tyrosine phosphatase type IVA 1 Enzyme IC50 6.52 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 6.27 DRUG MATRIX
Alpha-1A adrenergic receptor GPCR IC50 5.92 CHEMBL
Glutamate NMDA receptor Ion channel IC50 5.88 CHEMBL
Acrosin Enzyme Ki 5.64 CHEMBL
Protein S100-B Unclassified Kd 4.36 CHEMBL

External reference:

IDSource
4019043 VUID
N0000178948 NUI
D00834 KEGG_DRUG
140-64-7 SECONDARY_CAS_RN
4019043 VANDF
4019881 VANDF
C0030863 UMLSCUI
CHEBI:45081 CHEBI
PNT PDB_CHEM_ID
CHEMBL55 ChEMBL_ID
CHEMBL361506 ChEMBL_ID
DB00738 DRUGBANK_ID
CHEMBL935 ChEMBL_ID
D010419 MESH_DESCRIPTOR_UI
4735 PUBCHEM_CID
4167 INN_ID
673LC5J4LQ UNII
7994 RXNORM
2196 MMSL
5250 MMSL
7933 MMSL
d00030 MMSL
002971 NDDF
16826009 SNOMEDCT_US
31692006 SNOMEDCT_US
372699006 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Pentamidine Isethionate HUMAN PRESCRIPTION DRUG LABEL 1 13925-515 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 300 mg INTRAMUSCULAR ANDA 13 sections
Pentamidine Isethionate HUMAN PRESCRIPTION DRUG LABEL 1 13925-522 INHALANT 300 mg RESPIRATORY (INHALATION) ANDA 21 sections
pentamidine isethionate HUMAN PRESCRIPTION DRUG LABEL 1 23155-748 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 300 mg INTRAMUSCULAR ANDA 17 sections
Pentam 300 HUMAN PRESCRIPTION DRUG LABEL 1 63323-113 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 300 mg INTRAMUSCULAR NDA 13 sections
NebuPent Human Prescription Drug Label 1 63323-877 INHALANT 300 mg RESPIRATORY (INHALATION) NDA 12 sections